You may rember comedian Steven Phillips-Horst from our coverage of his web series about a campaign trail last year, Trailing. While the political climate has certainly changed since then, Phillips-Horst's odd, Christopher Guest-ish sense of humor has not. Phillips-Horst is part of the comedy duo Talk Hole, co-created by Eric Schwartau. Their new short film, Art Fair, which features SNL writer and OUT 100 honoree Julio Torres, as well as comedian Jacqueline Novak, takes a dry, tongue-in-cheek look at the bizarre, pretentious world of visual art. Talk Hole also hosts a monthly standup show in Manhattan.

You can watch all of Art Fair below:

We sat down with Phillips-Horst to talk about making Talk Hole's new film, their awesome cast, and how to make comedy in these dark, twisted political times.

OUT: Tell me about your monthly standup show at Talk Hole.

Steven Phillips-Horst: We’ve been doing it out of a karaoke lounge in Chinatown that is in the basement of a Chinese-Italian fusion restaurant. So you’ll really see that theme of two cultures coming together a lot in our work. And that ambiguity. We really try to find comfort in the ambiguity. It’s very intimate, very raw, very raucous. We’ve never booked a straight man.

Thank you for saying that.

I think they have enough of a voice as it is. Some people might say, “You have to go where the talent is.” But we’ve managed to find lots of women, and gay men, and trans people, and lesbians of all colors.

What do you look for in your lineup?

We consider ourselves curators. Some comedy shows will throw a bunch of people in a lineup and see what sticks. Our crowd is not typical. They don’t go to a bunch of comedy shows, per se. It’s more of a downtown crowd. A fashion crowd. An art crowd.

Which brings us to Art Fair. What was your inspiration?

We wanted to do a show about an art fair, and we had talked with NADA, which is the fair we shot it at. NADA has a couple shows each year—one in New York, one in Miami that happens during Basel. When I first went to Art Basel, I was just a kid of 22 or 23, and fashion hadn’t turned it into the circus with BMWs, Paris Hilton, and Jay Z. It was raw. So NADA is a smaller fair trying to ride the coattails of Basel, which is a bigger fair—tons of rich people go there. But in the art world it’s all about what’s next. What’s new. So the galleries that exhibit at NADA are smaller, and independent. If you’re a collector with his or her eye on what’s going to be big, you definitely want to go there, because there’s going to be these younger, fresher artists that haven’t sold out to the mainstream.

How did you end up meeting and casting Jacqueline and Julio Torres?

We asked comedians we love. Jacqueline Novak is a brilliant actress and comedian and incredible improviser—she just had her Comedy Central half hour, and she co-hosts a show with John Early, which is also in a basement in Manhattan. And then just from the comedy scene, just from going to shows, and performing at other people’s shows. I’ve been doing this for a couple years now. I’ve been meeting people, seeing who I like, just going to open mics. And people recommend people to you. Julio is a total weirdo. And then Max Wittert is an animator and standup comedian. He’s in High Maintenance this season, in the episode with Colby Keller. He’s a friend at the brunch.

That’s a big accomplishment.

It’s huge. Look out for me, I’m going to be playing a customer in the next season of Girls. Big TV shows are filled with people who are auditioning for the tiniest roles, and are thrilled to get them.

How did you write the film?

We would have an idea, for example, that Jacqueline and I would go hang out by a basketball hoop and blow smoke up each other’s asses. Or we’ll have a scene where you and Julio are talking about this piece, and maybe have some tension there. So we set up the scenarios and had some musts, like, make sure everyone says the word “bold.” So then we had all this footage, and these themes came to the surface, like access—being in, but out. Who gets to go? This happens at any event. It’s particularly subtle and pointed at art events, but the idea of “Who got in? Did you get in? Who’s here?” That pride when you see a person who is there; were they flown in? Are they just a hanger on?

As a comedian, what are your thoughts right now on the political climate?

In some ways nothing has changed, but in other ways everything has changed. I used to work in politics. I spent several years working on political campaigns.

You had that show, Trailing.

Yes, and the second season of Trailing is going to be coming out next year. I just finished writing all the scripts, which is great. But it was a struggle for me, because what is the world that I’m making fun of anymore? I don’t know if it still exists. I’ve worked on a couple Democratic campaigns, and it was people always being afraid—that classic Hillary idea of people going, “Should we tweet this? Should we tweet that? Oh, make sure there are no typos! Did you do the wrong thing? Offend the wrong person?” It’s this very carefully orchestrated world. And the Trump idea of politics is the complete opposite of that. When Fidel Castro died, he literally tweeted, “Fidel is dead!”

There’s really no joke to be made anymore because it’s so insane already.

Right, so the challenge now is to push satire really far. You would think it was a joke that, “Oh, I’m picking the head of an oil company to be Secretary of State!” No, that’s actually happening. It’s a twisted world, and I think Ivanka is a very interesting character at the center of it all. She really represents the emptiness of the current American dream. Which is building a lifestyle brand that’s meaningless, which is basically what she’s done. Her company says “Women Who Work,” and the work is “Women Who Work.” It’s just this weird circular logic that doesn’t going anywhere that she’s using to sell dresses. I heard a quote that was literally, “Shop my copywriter’s favorite looks.” And that’s not a Republican or Democrat ideal, that’s just what we’ve been building toward in our shark tank society. What scares me is that all just continues, and we buy it, and we keep going to Sweetgreen, and Aleppo burns. There’s tragedy in the world.